Issue 33, 2009
From the journal:

Dalton Transactions

Chiral diphosphinites derived from 2,2-biphosphole as a new class of stereodynamic ligands for enantioselective hydrogenation†

Emmanuel Robé,ab   Csaba Hegedüs,c   József Bakos,c   Jean-Claude Daranab  and  Maryse Gouygou*ab  

* Corresponding authors

a CNRS, LCC (Laboratoire de Chimie de Coordination), 205, route de Narbonne, France
E-mail: gouygou@lcc-toulouse.fr
Fax: +33 1 61 55 30 03
Tel: +33 5 61 33 31 74

b Université de Toulouse, UPS, INPT, LCC, France

c Institute of Chemistry, University of Pannonia, H-8201 Veszprém, PO Box 158, Hungary

Abstract

New stereodynamic diphosphinites derived from 2,2′-biphosphole, were synthesised by introduction of a linker obtained from chiral diols between the two phosphorus atoms and used for catalytic hydrogenation through a dual chirality control induced by Rh-coordination. The application of these ligands in hydrogenation of dimethyl itaconate shows that the enantioselectivity strongly depends on steric and electronic properties of the chiral linker whereas the sense of enantioselection is determined by the configuration of these stereocentres. These stereodynamic diphosphinites induce higher enantioselectivities than the analogous stereodynamic diphosphanes derived from 2,2-biphosphole.

Graphical abstract: Chiral diphosphinites derived from 2,2-biphosphole as a new class of stereodynamic ligands for enantioselective hydrogenation

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Article information

DOI
https://doi.org/10.1039/B900829B
Article type
Paper
Submitted
14 Jan 2009
Accepted
28 May 2009
First published
07 Jul 2009

Dalton Trans., 2009, 6528-6535

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Chiral diphosphinites derived from 2,2-biphosphole as a new class of stereodynamic ligands for enantioselective hydrogenation

E. Robé, C. Hegedüs, J. Bakos, J. Daran and M. Gouygou, Dalton Trans., 2009, 6528 DOI: 10.1039/B900829B

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